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Pure Appl. Chem., 2005, Vol. 77, No. 7, pp. 1131-1137

Total synthesis of zincophorin

Janine Cossy, Christophe Meyer, Magali Defosseux and Nicolas Blanchard

Laboratoire de Chimie Organique, Associé au CNRS, ESPCI, 10 rue Vauquelin 75231 Paris Cedex 05, France

Abstract: A total synthesis of the naturally occurring ionophore zincophorin has been realized. The key steps are an intramolecular oxymercuration of a cyclopropanemethanol for the elaboration of the tetrahydropyran ring and a Carroll–Claisen rearrangement to control the configuration of the double bond at C20–C21 as well as the stereogenic center at C21.